HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-pent-4-enyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 68613368 | HCID 68613368 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-pent-4-enyl ester | HCID 68614182 | 85.6% |
Reaction Steps
Under nitrogen, to a stirring solution of 240 mg of palladium acetate (1.1 mmol) in 20 mL of de-gassed dichloromethane, was added 460 uL of triethylamine (3.3 mmol), and 5.33 mL of triethylsilane (33 mmol). After stirring at rt for 15 min, 7.3 g of intermediate 17-2 in 25 mL of de-gassed dichloromethane was added in. The resulting solution was stirred at rt overnight. The reaction mixture was passed through a celite pad, and the filtrate was concentrated and purified by flash column chromatography using DCM/MeOH (v/v 9/1) as eluent, giving colorless oil 4.55 g (85%). LC-MS: m/z=240.1 (ES−).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09163061B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-476ac76c5f4e4b88833b812ca9c75a5e |
| Source note | uspto-grants-2015_10 |